DE1768847B1 - Verfahren zur Abtrennung von d-trans-Chrysanthemumcarbonsaeure - Google Patents
Verfahren zur Abtrennung von d-trans-ChrysanthemumcarbonsaeureInfo
- Publication number
- DE1768847B1 DE1768847B1 DE19681768847 DE1768847A DE1768847B1 DE 1768847 B1 DE1768847 B1 DE 1768847B1 DE 19681768847 DE19681768847 DE 19681768847 DE 1768847 A DE1768847 A DE 1768847A DE 1768847 B1 DE1768847 B1 DE 1768847B1
- Authority
- DE
- Germany
- Prior art keywords
- trans
- chrysanthemum
- acid
- monocarboxylic acid
- ester
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000000926 separation method Methods 0.000 title claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 8
- XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical compound CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 claims description 7
- 150000002763 monocarboxylic acids Chemical class 0.000 claims description 6
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 5
- 238000005755 formation reaction Methods 0.000 claims description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- -1 benzylfurylmethyl alcohol Chemical compound 0.000 claims description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims description 2
- IVGYSSJKFLEVIX-UHFFFAOYSA-N (-(E)-Pyrethrolone Natural products CC1=C(CC=CC=C)C(=O)CC1O IVGYSSJKFLEVIX-UHFFFAOYSA-N 0.000 claims 2
- IVGYSSJKFLEVIX-SNAWJCMRSA-N (E)-pyrethrolone Chemical compound CC1=C(C\C=C\C=C)C(=O)CC1O IVGYSSJKFLEVIX-SNAWJCMRSA-N 0.000 claims 2
- ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 claims 1
- FMTFEIJHMMQUJI-NJAFHUGGSA-N 102130-98-3 Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C FMTFEIJHMMQUJI-NJAFHUGGSA-N 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 claims 1
- VQXSOUPNOZTNAI-UHFFFAOYSA-N Pyrethrin I Natural products CC(=CC1CC1C(=O)OC2CC(=O)C(=C2C)CC=C/C=C)C VQXSOUPNOZTNAI-UHFFFAOYSA-N 0.000 claims 1
- 240000004460 Tanacetum coccineum Species 0.000 claims 1
- VXSIXFKKSNGRRO-MXOVTSAMSA-N [(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate;[(1s)-2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-3-[(e)-3-methoxy-2-methyl-3-oxoprop-1-enyl Chemical class CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1.CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VXSIXFKKSNGRRO-MXOVTSAMSA-N 0.000 claims 1
- ROVGZAWFACYCSP-MQBLHHJJSA-N [2-methyl-4-oxo-3-[(2z)-penta-2,4-dienyl]cyclopent-2-en-1-yl] (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-MQBLHHJJSA-N 0.000 claims 1
- 229940024113 allethrin Drugs 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 230000007775 late Effects 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 claims 1
- ROVGZAWFACYCSP-VUMXUWRFSA-N pyrethrin I Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-VUMXUWRFSA-N 0.000 claims 1
- 229940070846 pyrethrins Drugs 0.000 claims 1
- 239000002728 pyrethroid Substances 0.000 claims 1
- 229940015367 pyrethrum Drugs 0.000 claims 1
- CXBMCYHAMVGWJQ-UHFFFAOYSA-N tetramethrin Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCN1C(=O)C(CCCC2)=C2C1=O CXBMCYHAMVGWJQ-UHFFFAOYSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 6
- 241000723353 Chrysanthemum Species 0.000 description 5
- 235000007516 Chrysanthemum Nutrition 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- XLOPRKKSAJMMEW-SFYZADRCSA-N (+)-trans-chrysanthemic acid Chemical compound CC(C)=C[C@@H]1[C@@H](C(O)=O)C1(C)C XLOPRKKSAJMMEW-SFYZADRCSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 150000000185 1,3-diols Chemical class 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR113581A FR1536458A (fr) | 1967-07-07 | 1967-07-07 | Procédé d'obtention de l'acide d-trans chrysanthémique |
| FR113580A FR92748E (fr) | 1966-01-26 | 1967-07-07 | Nouveaux composés optiquement actifs et procédé pour leur utilisation au dédoublement de produits racémiques. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1768847B1 true DE1768847B1 (de) | 1972-07-06 |
Family
ID=26177941
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681768847 Pending DE1768847B1 (de) | 1967-07-07 | 1968-07-05 | Verfahren zur Abtrennung von d-trans-Chrysanthemumcarbonsaeure |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3646118A (cs) |
| JP (1) | JPS4933197B1 (cs) |
| AT (1) | AT284081B (cs) |
| CH (1) | CH493457A (cs) |
| CS (1) | CS166705B2 (cs) |
| DE (1) | DE1768847B1 (cs) |
| DK (1) | DK138222B (cs) |
| FR (1) | FR1536458A (cs) |
| GB (1) | GB1220160A (cs) |
| NL (1) | NL163769C (cs) |
| OA (1) | OA02844A (cs) |
| PL (1) | PL72564B1 (cs) |
| SE (2) | SE351207B (cs) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3739019A (en) * | 1969-07-02 | 1973-06-12 | Sumitomo Chemical Co | Preparation of optically active trans chrysanthemic acid |
| DE2800922A1 (de) * | 1978-01-10 | 1979-07-19 | Bayer Ag | Verfahren zur trennung stereoisomerer vinylcyclopropancarbonsaeuren |
| FR2443452A1 (fr) * | 1978-12-08 | 1980-07-04 | Roussel Uclaf | Nouveau procede de dedoublement de l'acide dl cis et dl trans chrysanthemique |
| US4229593A (en) * | 1979-05-29 | 1980-10-21 | Fmc Corporation | Method to prepare (+)-cis-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropanecarboxylic acid |
| JPS56108737A (en) * | 1980-01-31 | 1981-08-28 | Sumitomo Chem Co Ltd | Method for obtaining optically active 2*22dimethyll33 2*22 dichlorovinyl cyclopropanecarboxylic acid |
| HU188335B (en) * | 1982-11-25 | 1986-04-28 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt,Hu | Process for preparing optically active derivatives of cyclopropane-carboxylic acid |
| IT1194152B (it) * | 1983-03-07 | 1988-09-14 | Secifarma Spa | Procedimento di risoluzione enantiomerica di miscele di acidi d- e l-6-metossi-alfa-metil-2-naftalenacetici ed agenti di risoluzione per detto procedimento |
| DE69906607T2 (de) | 1998-01-29 | 2003-12-18 | Sumitomo Chemical Co., Ltd. | Verfahren zur Herstellung von optisch aktiven Chrysanthemumsäure |
-
1967
- 1967-07-07 FR FR113581A patent/FR1536458A/fr not_active Expired
-
1968
- 1968-07-02 DK DK324068AA patent/DK138222B/da not_active IP Right Cessation
- 1968-07-04 CH CH997668A patent/CH493457A/fr not_active IP Right Cessation
- 1968-07-04 OA OA53313A patent/OA02844A/xx unknown
- 1968-07-05 SE SE09347/68A patent/SE351207B/xx unknown
- 1968-07-05 JP JP43046620A patent/JPS4933197B1/ja active Pending
- 1968-07-05 US US742532A patent/US3646118A/en not_active Expired - Lifetime
- 1968-07-05 CS CS4965A patent/CS166705B2/cs unknown
- 1968-07-05 NL NL6809499.A patent/NL163769C/xx not_active IP Right Cessation
- 1968-07-05 SE SE07105/71A patent/SE359087B/xx unknown
- 1968-07-05 DE DE19681768847 patent/DE1768847B1/de active Pending
- 1968-07-06 PL PL1968127971A patent/PL72564B1/pl unknown
- 1968-07-08 AT AT656268A patent/AT284081B/de active
- 1968-07-08 GB GB32550/68A patent/GB1220160A/en not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| DK138222C (cs) | 1979-01-08 |
| GB1220160A (en) | 1971-01-20 |
| CS166705B2 (cs) | 1976-03-29 |
| NL6809499A (cs) | 1969-01-09 |
| SE351207B (cs) | 1972-11-20 |
| AT284081B (de) | 1970-08-25 |
| JPS4933197B1 (cs) | 1974-09-05 |
| NL163769C (nl) | 1980-10-15 |
| CH493457A (fr) | 1970-07-15 |
| OA02844A (fr) | 1970-12-15 |
| SE359087B (cs) | 1973-08-20 |
| DK138222B (da) | 1978-07-31 |
| FR1536458A (fr) | 1968-08-16 |
| PL72564B1 (en) | 1974-08-30 |
| US3646118A (en) | 1972-02-29 |
| NL163769B (nl) | 1980-05-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 |